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How to Succeed in the Era of Virtual Selling

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The exceptions of today are fast becoming the norms of tomorrow. Previously, pursuing a sale entirely from a virtual setting was a practise reserved for extenuating circumstances. Today, those circumstances have become commonplace. As a result, sales leaders face the challenge of adapting to a new environment.

Though this change was likely always on the horizon, recent global events have acted as an accelerant. Therefore, success means moving at this intensified pace of change while also acknowledging that this new mode of selling is not a passing one but is instead a permanent one. Consider that 67% of the stakeholder’s buying journey already occurs on digital channels, according to research from Deloitte. Even when economic factors return to pre-crisis levels, many customers will have acclimated to a new reality characterised by virtual sales engagements. Developing virtual selling skills now positions organisations for success in what will prove to be a challenging present and a changed future.

Here, we offer guidance for selling in the era of virtual engagement by examining:

    1. Why it matters
    2. How it happens
    3. Where it’s going

Why Virtual Selling Matters

The relevance of selling in a virtual setting is self-evident given recent global health and economic conditions. However, a closer look at virtual selling reveals several unexpected benefits that embrace the evolving nature of business as we approach the second quarter of the 21st century.

Understanding these benefits is important because they illustrate why virtual selling is more than a continuity plan for difficult times. They show why this approach to engaging customers is critical as competitive conditions intensify, the need for quality talent grows, and operational costs increase.

Expand the Addressable Market

Increasingly, delivering on revenue goals requires the ability to access a wider geographical region. This truth is coming into focus as businesses begin to see competitive threats encroaching from a distance because rivals are seeking to capitalise on opportunities once thought to be out of their reach.

Forward-thinking leaders are responding with their own expansive approach to the market by using technology to reach more customers. This idea is quickly rising to the level of an imperative, given that “the emerging economies’ share of Fortune Global 500 companies will probably jump to more than 45 percent by 2025, up from just 5 percent in 2000,” according to research from McKinsey.

Simply put, the growth of tomorrow will not look like the growth of yesterday. Moreover, an estimated 70% of the companies scheduled to reach a revenue of $1 billion or more will come from emerging markets, according to the same data. Sales organisations can adopt this strategy with a sales approach that works from a distance. Doing so means adopting a new mindset. Leaders must move beyond the conventional thinking that seeks to pair the sales opportunity with the sales professional in closest geographic proximity to the customer. Instead, leaders should choose the sales professional that has the skillset and experience most suited to the customer’s needs even if that sales professional is located in a distant region. While unconventional, this approach makes intuitive sense because a sales professional’s acumen is more relevant than their address.

In this scenario, virtual selling skills are critical. If the sales professional has the capability to properly engage the customer through digital tools, the issue of distance becomes moot. With the right approach, the sales professional can do everything via video that they can do in person, including uncovering needs, attaining the status of a trusted advisor, and coalescing stakeholders.

Accelerate the Momentum of the Sale

Maintaining momentum is critical to winning the sale. Doing so is difficult when sales professionals must align schedules, arrange travel plans, and deal with unexpected changes to the customer’s availability. Virtual selling overcomes many of these challenges by creating an environment in which meetings can occur when they are needed.

As the customer’s priorities and needs change, the sales professional must be equipped to track and adjust. This flexibility has become particularly important as the business landscape has changed in recent years. Research from ATKearney shows that “two-thirds of companies have a strategy horizon of four years or less.” This reality translates into a more iterative process on the buyer’s side of the table. With virtual engagement, sales professionals have more of an opportunity to be part of this process without being subjected to the sidelines, an all too common outcome when a customer is regularly changing paths.

This quickening pace of change is also increasing the complexity of understanding the customer’s core challenges and goals. As a result, sales professionals need to develop “situational fluency,” which is the ability to discuss each buyer’s specific business issues, what is causing them, and which capabilities are needed to address those challenges for the customer. Developing this fluency means being able to effectively apply the immediacy of a virtual engagement. The more immersed the sales professional becomes in the customer’s journey, the more influential they become. In fact, research spanning more than 200 companies revealed that the “ability to shape customer journeys will become a decisive source of competitive advantage,” according to McKinsey.

The challenge for many sales professionals is to apply virtual tools in a way to goes beyond merely “checking in” throughout the journey. Effective sales professionals adjust their approach to fit within the constraints of the medium. They must continually ask questions without ever letting even a single assumption solidify into a fact. They become proactive in soliciting opinions and exploring the specifics behind different stakeholder needs.

Adjust the Business Model to New Economic Factors

Businesses continue to cut spending as global health concerns — and therefore business concerns — grow. Though many countries have rushed to solve the most immediate problems of the pandemic, the economic toll has become palpable. Resumption of normal business will take time given that our increasingly globalised economy demands a united recovery. Even as this recovery unfolds, many businesses will be reluctant to allocate depleted resources to travel expenses. Severe cost-avoidance measures will normalise as survival and business continuity become the predominant model.

Virtual selling capabilities embrace this immobilised environment by keeping sales professionals engaged in meaningful dialogues with customers. More importantly, virtual selling skills will serve selling organisations long after the upheavals of today have subsided. Erik Brynjolfsson, director of the MIT Initiative on the Digital Economy, articulated this idea succinctly when he explained in a Washington Post interview that “a shock like this that can change everything.” He continues, “It forces people to overcome the switching costs, figure out something new and say, ‘Hey, this is way better.’” Selling organisations are making this discovery as circumstances necessitate a jump off the diving board. In fact, many are learning that this mode of selling is not only impactful, but necessary as their competitors embrace selling virtually.

The unforeseen events of today are forcing both sales professionals and customers to accept a new mindset. This thinking is free of any lingering stigma associated with conducting business over virtual channels. Even customers who were once ambivalent about conducting critical conversations about business solutions over video are now accepting of the idea. This acceptance is unlikely to fade as remote work provisions persist throughout the year. This trend is not purely the result of the coronavirus pandemic. Consider that the number of companies offering remote work options increased threefold over the last two decades, according to research from The Society for Human Resource Management and Gallup. Current circumstances are not only introducing new norms they are accelerating existing ones.

How Virtual Selling Happens

While virtual selling offers the benefits discussed previously, it also presents new challenges. Customers are more likely to disengage. Developing meaningful connections becomes a steeper climb without the tactile environment of in-person meetings. These challenges are important to understand because they are different from those common to traditional, in-person selling.

Redrafting the playbook for virtual selling means developing an awareness of these pitfalls, a structured approach that is repeatable, and an understanding of the unique psychology underpinning difficult conversations that surface during customer challenges.

Gain a Full View of the Challenges

One of the key challenges inherent to virtual selling is the misuse of technology. It is easy to perceive the virtual setting as a one-way channel from the sales professional to the customer. In reality, the technology is better used as a two-way channel for exchanging and sharing information. The tendency to think of the virtual environment as a medium for presentation, rather than conversation, stems from the deceptively common cognitive bias known as functional fixedness.

Functional fixedness is the propensity to use an object in a traditional way when it could in fact be used more effectively in a different way. For example, imagine a person who needs to drive a screw into a wall but does not have a screwdriver. Functional fixedness tells us that the person might leave the job incomplete without realising that the dime in their pocket could be used to turn the screw. We suffer from the “mental block against using an object in a new way that is required to solve a problem,” according to psychologist Karl Duncker who first coined the term.

Many sales professionals approach virtual selling with a functional fixedness mindset in which the medium is used in a limiting way. Virtual engagements must be used to facilitate conversation on both sides rather than as a tool for the sales professional to merely present while the customer becomes a passive listener. By limiting our understanding of how a virtual setting can be used, we succumb to difficulties like:

    • Missing valuable rapport-building opportunities
    • Allowing environmental distractions to interrupt progress
    • Losing the collaborative environment that is critical to selling
    • Permitting the setting to undermine authenticity
    • Limiting instances of spontaneous discussions that reveal unexpected insights
    • Growing disengagement as customers come and go with ease
    Using the medium as an effective selling tool means first acknowledging the challenges it presents. Fortunately, many of these challenges stem from the functional fixedness bias that can be overcome by understanding how to use a virtual setting to its full potential.

    Develop a Repeatable Virtual Sales Plan

    Preventing a drift into unproductive and disorganised engagements requires a structured, repeatable plan. This step-by-step approach is critical because it prevents the backslide into conventional selling behaviours that are more appropriate for in-person engagements. Importantly, checklists are so effective they have broad-based adoption in high-stakes fields like healthcare. As surgeon and author Atul Gawande explains in his book The Checklist Manifesto, “Checklists seem able to defend anyone, even the experienced, against failure in many more tasks than we realised. They provide a kind of cognitive net. They catch mental flaws inherent in all of us — flaws of memory and attention and thoroughness.” For sales professionals working in a virtual setting, this checklist should spread across three main components: an introduction, a body, and a closing.


    Interaction does not flow as naturally in a virtual room. Stakeholders are often on mute, occasionally with their cameras off while multi-tasking, unless they are actively engaged. Therefore, it is the sales professional’s job to create an environment that is welcoming, engaging, and comfortable. Doing so means asking rapport-building questions to specific individuals that encourage them to take themselves off of mute. To get the customers on camera — an uncomfortable scenario for some — sales professionals should recognise a stakeholder who is on camera and encourage the others to follow suit. If all of the stakeholders have the camera off, the sales professional should preface their request by explaining that seeing everyone makes it easier to get to know the group.

    These steps allow the sales professional to transition into a formal opening in which they can introduce themselves and facilitate introductions while credentialising their organisation and team. Next, they should set the context with a recap of events, leading to the meeting and previous understanding of needs and if they have changed. Finally, the introduction should end by aligning everyone to the agenda by positioning the purpose of the meeting and checking for feedback.


    The body of the meeting is the sales professional’s opportunity to connect with the customer, understand their needs, and ultimately position the solution. In the early section of the body, there should be fewer slides, more eye contact, and close attention to the diagnosing of needs. Later in the process, the sales professional can begin to position recommendations and get more granular with the information provided. Finally, near the end, sales professionals should be sure to track where the common ground lies and share summaries of the discussion.

    Achieving these steps means developing and using the Six Critical Skills. These skills are important because they create a framework for the sales professional and serve to differentiate the sales professional from others in an increasingly commoditised market. They are developed through experience, sales coaching, and training. They must be refined throughout a sales rep’s career.

    The Six Critical Skills are:

    6 critical selling skills richardson

    To learn more about the 6 critical skills download the brief: Everything Begins with Soft Skills


    Virtual meetings often run short on time. As a result, the closing can become rushed as participants leave the meeting unannounced. Preventing this common outcome means applying the same level of organisation to the closing as one should the introduction and the body.

    Sales professionals must first summarise the outcomes of the discussion. This is an opportunity to emphasise value in a concise way. Next, gain commitment. Maintaining momentum requires setting next steps, which should include actions on the part of both the sales professional and the customer. Here, it is critical to check for alignment to ensure that everyone agrees on the path forward. The sales professional can think of the closing as an opportunity to lay the groundwork for the negotiation to come. In the negotiation phase, it will be critical to reach a mutually beneficial outcome. Therefore, sales professionals must anchor the value of their solution while making clear how the product or service fits the specific customer goals.

    Finally, sales professionals should be intentional in their attempt to leave a positive last impression by deepening rapport, restating their personal commitment, and demonstrating their confidence and positivity.

    Recalibrate for Uncomfortable Conversations

    Business conditions have worsened across all industries. This upheaval means that many sales professionals will be speaking with customers who are under stress. In these circumstances, it is difficult to pinpoint the specificity of the customer’s challenges because doing so requires asking difficult questions that surface uncomfortable truths.

    Many sales professionals shy away from such conversations. They fear that sensitive questions may appear accusatory or even admonishing. Such questions may seem in direct opposition to the idea of leaving the customer with a positive feeling about the relationship. Yet, avoiding these questions prevents the kind of solution positioning that addresses the nuances of the customer’s circumstances. Put simply, sensitive questions, though uncomfortable, are necessary. In fact, an aversion to sensitive questions “can be economically costly,” according to social science research from The University of Pennsylvania.

    The researchers worked with nearly 1,000 participants in their study and discovered that “question askers believe that asking sensitive questions will cause greater discomfort than they actually do, and they expect that asking sensitive questions will harm the respondent’s impression of them more than they actually do.” Their research is a powerful reminder that sensitive questions are the key to understanding the core of an issue. Without this understanding of the customer’s central issue, it is difficult for the sales professional to move forward. However, people have a strong, inherent aversion to exploring uncomfortable topics. In fact, “when explicitly incentivised to do so, individuals often refrain from asking sensitive questions,” according to the study, and “participants earned less money than was possible in this study because they avoided asking as many sensitive questions as they could have asked.”

    Sales professionals who venture to ask sensitive questions will be rewarded with detail that reveals the pain points the customer wants to resolve. To overcome the initial discomfort, sales professionals can preface the question by clarifying why they are about to ask the question and why the customer’s answers will enable the sales professional to deliver a more effective solution.

    Overcoming the difficulty of asking uncomfortable questions also requires superior preparation. This fact is counterintuitive because it is easy to envision virtual selling as a “push button” solution given that the engagement is free of travel logistics. However, sales professionals need a greater awareness of the benefits and drawbacks of the medium if they are to apply it to project professionalism while building credibility and rapport. It is difficult to build rapport virtually than face to face because we no longer have those natural moments — like riding the elevator together, walking down the hall, and eating lunch together — when business discussion often pauses and allows for more personal rapport building.

    Here, preparation means:

      • Managing expectations by sharing an agenda
      • Managing the environment by eliminating distractions
      • Planning materials carefully with clean, simple visuals
      • Testing your technology and preparing a backup plan in the event of failure

      Where Virtual Selling is Going

      Many forward-thinking business leaders do not view the upheavals of today as a mere interruption — they see them as an introduction. They understand that virtual selling will become an accepted practise as remote collaboration becomes normalised in a short period of time.

      More importantly, virtual selling is an approach that addresses the long term because it serves as a business continuity plan, a mode of communication that facilitates selling with agility and helps elevate sales professionals to the status of a trusted advisor as a result of close and regular contact with customers.

      Virtual Selling will Become a Business Continuity Plan

      Virtual selling represents a long-term business continuity plan for two reasons. First, a skill-based business continuity plan can be implemented fast. There is no need for auxiliary infrastructure or contingency supply chains.

      Relying on a skill-based contingency plan, however, requires broad-based buy-in from the sales professionals because “after a disruption, the factor that clearly distinguishes those companies that recover quickly, and even profitably, from those that falter is corporate culture,” according to Yossi Sheffi, MIT professor and author of The Resilient Enterprise: Overcoming Vulnerability for Competitive Advantage. In his work, Sheffi underscores the importance of a sentiment first shared by Southwest CEO Herb Kelleher, explaining that “the important thing is to take the bricklayer and make him understand that he’s building a home, not just laying bricks.” That is, sales professionals must understand that their participation in virtual selling training is part of a durable, long-term plan designed for not only the survival of the business, but their own survival as well.

      Second, virtual selling is scalable. This approach to selling can expand and contract with the marketplace because sales professionals will not be limited in their approach amid a downshift in travel spending. The ability to increase sales efforts without incurring additional travel is a considerable benefit given that annual global business travel spending totals approximately $1.5 trillion, according to the Global Business Travel Association, representing an estimated 55% of airline revenues.

      Virtual Selling will Equip Salespeople to Become Trusted Advisers Faster

      Sales professionals are more effective when the customer perceives them as a trusted adviser. This coveted status belongs to sales professionals who have a more sophisticated, in-depth understanding of the customer’s challenges and goals. A trusted advisor is equipped to address the complexities of the customer’s industry and therefore is consulted in advance of decisions.

      Virtual selling capabilities help sales professionals ascend to this level by leveraging the immediacy of a virtual connection to facilitate more interactions. With an understanding of how best to use the virtual medium, sales professionals are always prepared to jump into a discussion with a group of stakeholders and become an influential voice. This increased frequency of interaction helps blur the line that traditionally separates the stakeholders from the sales professional.

      Put simply, strong communication advances trust, and trust advances the sale. The connection between trust and positive, regular engagement is not only intuitive, it is also proven. Consider a massive 2015 Gallup study covering 2.5 million manager-led teams across 195 countries, which determined that “engagement improved when supervisors had some form of daily communication with direct reports.” This same principle applies to the relationship between customers and sales professionals. A virtual presence allows regular communication that is critical to establishing and maintaining the trust that precedes every sale.

      Virtual Selling will Become the Engine of the Agile Model

      Successful business models today are fundamentally different than those of previous decades. At one time, companies could sell a product and build revenues behind protective barriers. These barriers insulated the company from threats. The high cost of technology, long innovation periods, and developmental lead time all meant that competitors had many walls to scale if they wanted to grab market share. Those walls have fallen. What remains is the agile approach.

      An agile model focuses on collaboration and responsiveness to change rather than adhering to a single, unchanging plan. This fluidity perfectly matches the customer’s dynamic buying journey in which movement starts, stops, and sometimes even reverses. In this setting, customer conversations no longer follow a logical progression. Questioning for needs, floating ideas, and positioning value are tightly woven and appear in every customer dialogue. Agility in selling means flexing and using different skills when and where you need them.

      Virtual selling fits this model because it maintains communication during the critical periods that tend to unfurl in the periods between traditional in-person meetings. In these important “in-between” periods, sales professionals have an opportunity to understand the buying factors that contribute to the customer’s buying decisions. A virtual connection also enables the sales professional to take the iterative steps toward building consensus and even exploring the white space within an existing customer account.

      Adapting to a Changed Environment

      The intense circumstances of today have given leaders a much-needed push toward virtual selling. They are using it to the fullest extent to expand the addressable market, accelerate the sale, and embrace the economic realities of today. Building the capabilities to sell virtually means:

        1. Understanding the challenges inherent to virtual selling
        2. Developing a repeatable, three-part plan for structuring virtual conversations
        3. Formulating an approach to uncomfortable conversations in a challenging economy
      Selling organisations with the foresight to take the next step can expect benefits that exceed the here and now. As MIT professor and author Yossi Sheffi remarks, “The rewards for building a resilient organisation are substantial. The ‘hardened’ enterprise will be able to not only withstand all manner of disruption but also increase its competitiveness.”
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